Hidden Heptacyclic Chiral N-Acyl Iminium Ions: a New Entry to Enantioenriched Polycyclic Azepanes and Azocanes by Superacid-Promoted Intramolecular Pictet-Spengler Reaction

Yasmin Reviriot (1) , Bastien Michelet (2) , Rodolphe Beaud (1) , Agnès Martin-Mingot (2) , Frédéric Guégan (2) , Sébastien Thibaudeau (2) , Jean Rodriguez (1) , Damien Bonne (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 IC2MP [Poitiers] - Institut de chimie des milieux et matériaux de Poitiers [UMR 7285]

Enantioenriched complex fused-tricyclic azepanes or bridged-polycyclic azocanes were constructed via a two-step sequence involving an enantioselective organocascade followed by superacid activation of the domino adduct. The activated oxa-bridged azepane acts as a key hidden heptacyclic chiral N-acyl iminium ion triggering a chemo- and diastereoselective intramolecular mono- or di-arylation.

Mots clés: azocane; azepane; N-acyliminium ion; organocatalysis; superacid

Domaines: Chimie organique

Yasmin Reviriot, Bastien Michelet, Rodolphe Beaud, Agnès Martin-Mingot, Frédéric Guégan, et al.. Hidden Heptacyclic Chiral N-Acyl Iminium Ions: a New Entry to Enantioenriched Polycyclic Azepanes and Azocanes by Superacid-Promoted Intramolecular Pictet-Spengler Reaction. Chemistry - A European Journal, 2022, 28 (25), pp.e202200432. ⟨10.1002/chem.202200432⟩. ⟨hal-03769652⟩